Tetrabutylammonium Fluoride → HCID 118036952, compound

HRID 1777927Notes

Reaction equation

HRID 1777927 reaction equation
[Si]([O:18][CH:19]1[C:28]2[C:23](=[N:24][C:25]([CH:29]([O:32][CH3:33])[O:30][CH3:31])=[CH:26][CH:27]=2)[N:22]([C:34]([NH:36][C:37]2[CH:42]=[CH:41][C:40]([C:43]#[N:44])=[CH:39][N:38]=2)=[O:35])[CH2:21][CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:43]([C:40]1[CH:41]=[CH:42][C:37]([NH:36][C:34]([N:22]2[C:23]3[C:28](=[CH:27][CH:26]=[C:25]([CH:29]([O:32][CH3:33])[O:30][CH3:31])[N:24]=3)[CH:19]([OH:18])[CH2:20][CH2:21]2)=[O:35])=[N:38][CH:39]=1)#[N:44]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131734780HCID 131734780, compound2×

Product 1

HCID 118036952HCID 118036952, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (racemic) 4-((tert-butyldiphenylsilyl)oxy)-N-(5-cyanopyridin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 37Y, 30 mg, 0.049 mmol) in THF (0.3 ml) was treated with TBAF (1 M in THF, 0.054 ml, 0.054 mmol) and stirred at room temperature for 2 h. The reaction mixture was partitioned between DCM and sat. aq. NaHCO3. The aq. layer was extracted with DCM (2×). The combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum. The crude material was purified by normal phase chromatography (4 g silica gel cartridge, heptanes/EtOAc 100:0 to 10:90) to give the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 13.93 (s, 1H), 8.76-8.81 (m, 1H), 8.19-8.27 (m, 2H), 7.95 (d, 1H), 7.26 (d, 1H), 5.71 (d, 1H), 5.39 (s, 1H), 4.67-4.75 (m, 1H), 3.96-4.01 (m, 2H), 3.38 (d, 6H), 2.01-2.10 (m, 1H), 1.79-1.90 (m, 1H).

Workup

  1. customThe reaction mixture was partitioned between DCM and sat. aq. NaHCO3
  2. extractionThe aq. layer was extracted with DCM (2×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude material was purified by normal phase chromatography (4 g silica gel cartridge, heptanes/EtOAc 100:0 to 10:90)

Sources & evidence

ORD record
ord-ae302ad63b394771baa1157227099031
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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